Wellington, Kevin WKolesnikova, NI2012-06-292012-06-292012-05Wellington, KW and Kolesnikova, NI. 2012. A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity. Bioorganic and Medical Chemistry, vol. 20(14), pp 4472-44810968-0896http://www.sciencedirect.com/science/article/pii/S0968089612004026http://hdl.handle.net/10204/5958Copyright: 2012 Elsevier. This is the pre-print version of the work. The definitive version is published in Bioorganic and Medical Chemistry, vol. 20(14), pp 4472-4481Nuclear monoamination of a 1,4-naphthohydroquinone with primary aromatic amines was catalysed by the commercial laccase, Novozym 51003, from Novozymes to afford aminonaphthoquinones. The synthesis was accomplished by reacting a mixture of the primary amine and 1,4-naphthohydroquinone in succinate-lactate buffer and a co-solvent, dimethylformamide, under mild reaction conditions in a vessel open to air at pH 4.5 and pH 6.0. Anticancer screening showed that the aminonaphthoquinones exhibited potent cytostatic effects particularly against the UACC62 (melanoma) cancer cell line (GI50 = 3.98-7.54 µM). One compound exhibited potent cytostatic effects against both the TK10 (renal) and the UACC62 (melanoma) cancer cell line. The cytostatic effects of this compound (GI50 = 8.38 µM) against the TK10 cell line was almost as good as that of the anticancer aganet, etoposide (GI50 = 7.19 µM). Two compounds exhibited potent cytostatic effects against both the UACC62 (melanoma) and the MCF7 (breast) cancer cell lines. The total growth inhibition (TGI) of most of the compounds was better than that of etoposide against the UACC62 cell line. Three compounds (TGI = 7.17-7.94 µM) exhibited potent cytostatic effects against the UACC62 cell line which was 7 to 8-fold better than that of etoposide (TGI = 52.71 µM). The aminonaphthoquinones exhibit moderate to weak cytotoxic effects against a normal HeLa cell line. The results are encouraging for further study of the aminonaphthoquinones for their application in anticancer therapy.enBiocatalysisLaccaseOxidative enzymesGreen chemistry1,4-naphthohydroquinonesPrimary aminesMonoaminationAnticancer agentsCytostatic effectsCytotoxic effectsArticleWellington, K. W., & Kolesnikova, N. (2012). A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity. http://hdl.handle.net/10204/5958Wellington, Kevin W, and NI Kolesnikova "A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity." (2012) http://hdl.handle.net/10204/5958Wellington KW, Kolesnikova N. A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity. 2012; http://hdl.handle.net/10204/5958.TY - Article AU - Wellington, Kevin W AU - Kolesnikova, NI AB - Nuclear monoamination of a 1,4-naphthohydroquinone with primary aromatic amines was catalysed by the commercial laccase, Novozym 51003, from Novozymes to afford aminonaphthoquinones. The synthesis was accomplished by reacting a mixture of the primary amine and 1,4-naphthohydroquinone in succinate-lactate buffer and a co-solvent, dimethylformamide, under mild reaction conditions in a vessel open to air at pH 4.5 and pH 6.0. Anticancer screening showed that the aminonaphthoquinones exhibited potent cytostatic effects particularly against the UACC62 (melanoma) cancer cell line (GI50 = 3.98-7.54 µM). One compound exhibited potent cytostatic effects against both the TK10 (renal) and the UACC62 (melanoma) cancer cell line. The cytostatic effects of this compound (GI50 = 8.38 µM) against the TK10 cell line was almost as good as that of the anticancer aganet, etoposide (GI50 = 7.19 µM). Two compounds exhibited potent cytostatic effects against both the UACC62 (melanoma) and the MCF7 (breast) cancer cell lines. The total growth inhibition (TGI) of most of the compounds was better than that of etoposide against the UACC62 cell line. Three compounds (TGI = 7.17-7.94 µM) exhibited potent cytostatic effects against the UACC62 cell line which was 7 to 8-fold better than that of etoposide (TGI = 52.71 µM). The aminonaphthoquinones exhibit moderate to weak cytotoxic effects against a normal HeLa cell line. The results are encouraging for further study of the aminonaphthoquinones for their application in anticancer therapy. DA - 2012-05 DB - ResearchSpace DP - CSIR KW - Biocatalysis KW - Laccase KW - Oxidative enzymes KW - Green chemistry KW - 1,4-naphthohydroquinones KW - Primary amines KW - Monoamination KW - Anticancer agents KW - Cytostatic effects KW - Cytotoxic effects LK - https://researchspace.csir.co.za PY - 2012 SM - 0968-0896 T1 - A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity TI - A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity UR - http://hdl.handle.net/10204/5958 ER -